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Work craving theory addresses how work-addicted individuals direct great emotion-regulatory efforts to weave their addictive web of working. They crave work for two main emotional incentives: to overcompensate low self-worth and to escape (i.e., reduce) negative affect, which is strategically achieved through neurotic perfectionism and compulsive working. Work-addicted individuals" strong persistence and self-discipline with respect to work-related activities suggest strong skills in volitional action control. However, their inability to disconnect from work implies low volitional skills. How can work-addicted individuals have poor and strong volitional skills at the same time? To answer this paradox, we elaborated on the relevance of two different volitional modes in work craving: self-regulation (self-maintenance) and self-control (goal maintenance). Four hypotheses were derived from Wojdylo- work craving theory and Kuhl- self-regulation theory: (H1) Work craving is associated with a combination of low self-regulation and high self-control. (H2) Work craving is associated with symptoms of psychological distress. (H3) Low self-regulation is associated with psychological distress symptoms. (H4) Work craving mediates the relationships between self-regulation deficits and psychological distress symptoms at high levels of self-control. Additionally, we aimed at supporting the discriminant validity of work craving with respect to work engagement by showing their different volitional underpinnings. Results of the two studies confirmed our hypotheses: whereas work craving was predicted by high self-control and low self-regulation and associated with higher psychological distress, work engagement was predicted by high self-regulation and high self-control and associated with lower symptoms of psychological distress. Furthermore, work styles mediated the relationship between volitional skills and symptoms of psychological distress. Based on these new insights, several suggestions for prevention and therapeutic interventions for work-addicted individuals are proposed.